Born and raised in Rahway, New Jersey, Caldwell was an outstanding athlete, lettering in wrestling, football, and baseball at Rahway High School. A two-time All-Region football player, his true passion shone on the wrestling mats, where he achieved an impressive record of 148-4—with just three losses as a freshman—and earned three NJSIAA championships. Today, his dedication to the sport continues as he channels his expertise into youth wrestling classes and training, inspiring the next generation of athletes to excel both on and off the mat.